Abstract
The aziridation of 2-R-4,6-bis(trinitromethyl)-1,3,5-triazines containing electron-donor substituents has been studied. It was found that the corresponding 4-azido-2-dialkylamino-6-trinitromethyl-1,3,5-triazines are formed when R = NMe2, NEt2. When R = O−NMe4 + a novel reaction route was discovered leading to the tetramethylammonium salt of 5-polynitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one which is formed as a result of azido-tetrazole and lactim-lactam tautomeric conversion. Denitration of this salt at the trinitromethyl group occurs with retention of the tetrazolo-1,3,5-triazine structure. An X-ray analysis was carried out for the denitration product which was the dipotassium salt of 5-dinitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one.
Similar content being viewed by others
REFERENCES
A. V. Shastin, T. I. Godovikova, S. P. Golova, V. S. Kuz’min, L. I. Khmel’nitskii, and B. L. Korsunskii, Mendeleev Commun., 17 (1995).
A. V. Shastin, T. I. Godovikova, S. P. Golova, L. I. Khmel’nitskii, and B. L. Korsunskii, Khim. Geterotsikl. Soedin., 674 (1995).
A. V. Shastin, T. I. Godovikova, S. P. Golova, M. V. Povorin, D. E. Dmitriev, M. O. Dekaprilevich, Yu. A. Strelenko, Yu. T. Struchkov, L. I. Khmel’nitskii, and B. L. Korsunskii, Khim. Geterotsikl. Soedin., 679 (1995).
A. V. Shastin, T. I. Godovikova, S. P. Golova, L. I. Khmel’nitskii, and B. L. Korsunskii, Khim. Geterotsikl. Soedin., 1254 (1997).
A. V. Shastin, T. I. Godovikova, and B. L. Korsunskii, Khim. Geterotsikl. Soedin., 1404 (1998).
A. V. Shastin, T. I. Godovikova, and B. L. Korsunskii, Khim. Geterotsikl. Soedin., 76 (1999).
A. A. Gidaspov, V. V. Bakharev, and Yu. N. Bulychev, Khim.-Farm. Zh., 34, No.7, 6 (2000).
A. V. Shastin, T. I. Godovikova, and B. L. Korsunskii in: Papers of the First International Conference of the Chemistry and Biological Activity of Nitrogen Heterocycles and Alkaloids [in Russian], Vol. 2, Moscow (2001), p. 336.
A. V. Shastin, T. I. Godovikova, and B. L. Korsunskii in: Papers of the First International Conference of the Chemistry and Biological Activity of Nitrogen Heterocycles and Alkaloids [in Russian], Vol. 2, Moscow (2001), p. 338.
V. Ya. Pochinok, L. F. Avramenko, T. F. Grigorenko, and V. N. Skopenko, Usp. Khim., 44, 1028 (1975).
V. Ya. Pochinok, Usp. Khim. 45, 354 (1976).
V. P. Krivolapov, E. B. Nikolaenkova, and V. P. Mamaev, Izv. Akad. Nauk, Ser. Khim., 491 (1998).
E. Kessenich, K. Polborn, and A. Schulz, Inorg. Chem., 40, 1102 (2001).
D. J. Glover and M. J. Kamlet, J. Org. Chem., 26, 4734 (1961).
V. A. Ostrovskii and V. S. Poplavskii, Synthesis of Heterocyclic Compounds [in Russian], Lensovet Technical Institute, Leningrad (1985), p. 5.
D. H. R. Barton and W. D. Ollis (editors), Comprehensive Organic Chemistry [Russian translation], Khimiya, Vol. 8, Moscow (1985), p. 434.
S. S. Novikov, G. A. Shvekhgeimer, V. V. Sevost’yanova, and V. A. Shlyapochnikov, The Chemistry of Aliphatic and Alicyclic Nitrocompounds [in Russian], Khimiya, Moscow (1974), p. 330.
I. V. Tselinskii, I. V. Shugalei, and M. B. Shcherbinin, The Physical Chemistry of Nitrocompounds. The Geometry and Spectroscopy of Nitrocompounds [in Russian], Lensovet Technical Institute, Leningrad (1985), p. 35.
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 259–266, February, 2005.
Rights and permissions
About this article
Cite this article
Fedorov, B.S., Fadeev, M.A., Gidaspov, A.A. et al. Condensed Tetrazolo-1,3,5-triazines. 1. Synthesis of 5-Polynitromethyltetrazolo[1,5-a]-1,3,5-triazin-7-one Salts. Chem Heterocycl Compd 41, 228–234 (2005). https://doi.org/10.1007/s10593-005-0132-5
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-005-0132-5